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Communication | Special issue | Vol 86, No. 1, 2012, pp.133-138
Published online, 23rd July, 2012
DOI: 10.3987/COM-12-S(N)28
Nickel-Catalyzed Borylation of Aryl Halides with 4,4,6-Trimethyl-1,3,2-dioxaborinane

Miki Murata,* Yosuke Sogabe, Takeshi Namikoshi, and Shinji Watanabe

*Department of Materials Science and Engineering, Kitami Institute of Technology, Koen-cho 165, Kitami, Hokkaido 090-8507, Japan

Abstract

The nickel-catalyzed borylation of aryl iodides and bromides with 4,4,6-trimethyl-1,3,2-dioxaborinane was achieved. The mild reaction conditions employed allowed for the inclusion of common functional groups in aryl halides to be tolerated. A DFT study on the catalytic cycle shows that C–B bond formation occurs through σ-bond metathesis between dialkoxyborane and arylnickel(II) halide intermediates.